Jets GM Cheveldayoff refuses to rest on last season’s laurels

Elliotte Friedman joins Tim and Sid to discuss how Winnipeg Jets will have some tough roster decisions when it comes to contracts in the near future.

When the Winnipeg Jets re-signed the most patient general manager in the National Hockey League this time last year, some people wondered why.

Kevin Cheveldayoff’s team had just missed the playoffs for the fifth time in six seasons since it relocated from Atlanta and had yet to win a playoff game as the Jets. Now, we wonder if the Jets will win the Stanley Cup next spring and end Canada’s 25-year championship drought. The Jets are that good and Cheveldayoff’s biggest challenge is keeping his talented team together under the salary cap.

After a breakthrough 114-point campaign, Cheveldayoff would have been named NHL General Manager of the Year in any season that didn’t include the Vegas Golden Knights’ miracle. The Jets knocked off the Presidents’ Trophy-winning Nashville Predators in the second round of the Western Conference playoffs before getting run over by the Knights in the conference final. Vegas’s George McPhee was named the league’s top GM.

When Sportsnet sat down this week with Cheveldayoff at the Young Stars tournament in Penticton, B.C., we learned that his summer wasn’t much happier than all those years when the Jets were finished in April.

Sportsnet: Did last season feel like vindication for you, the reward for those years of patient building?

Cheveldayoff: Honestly, we really haven’t accomplished anything yet. We set out to try to win a championship, and until we get that… that’s really what it’s all about here. Last season was fun. The ride was great. It was a great experience for the players and a great experience for the fans.

From a euphoria standpoint, the city went crazy. But internally, there’s only so much satisfaction you take when you don’t win. Maybe it’s unfortunate you don’t relish some of those smaller victories, but it’s hard to win and that’s what we set out to achieve.

Sportsnet: But you orchestrated a 27-point improvement. You didn’t reflect on that with satisfaction?

Cheveldayoff: You have to move forward or you get left behind in this game. As an organization, certainly it was exciting and you never want to diminish that. But to say that we’ve achieved anything yet… that’s what it’s all about.

Sportsnet: Have you thought much about that Vegas series and what could have gone differently for your team?

Cheveldayoff: We had a hard-fought series against Nashville. They’re such a great team. Maybe if we had won Game 6, maybe that would have given us a few days to rest and recuperate. But you’ve got to win against the teams that are in front of you at that time, and we caught a very hot Vegas team.

Sportsnet: There’s a lot of talk now about the Jets being in their ‘window’ to win a Stanley Cup. Do you believe in windows?

Cheveldayoff: I believe you have to try to build something. But I believe you have to continue to build to maintain it. Drafting and developing isn’t just something a team does when an organization is trying to build up its team.

One thing that can make you a successful organization is continuous drafting and developing. That’s where it starts. It starts with this Penticton tournament, and starts with the (minor-league) Moose, trying to develop two or three players each and every year.

Sportsnet: But your best forward, Blake Wheeler, just turned 32 and top defenceman Dustin Byfuglien is 33. Even with all your excellent, young players, don’t you need to do everything you can to win in the next two or three seasons?

Cheveldayoff: You do what you can do. There’s been that level or urgency, really, from Day 1. But I can’t just manufacture a young player to do something he’s not ready to do. We traded a first-round pick at the deadline (last season) because there was an opportunity we wanted to jump at in getting Paul Stastny.

You evaluate what’s in front of you. You can say whatever you want and want to do this or want to do that, but if the opportunity is not right, you can’t do it. I think the urgency is there all the time to try to win.

Sportsnet: How do you keep your team together under the salary cap when players like Patrik Laine and Kyle Connor come out of their entry-level contracts after this season?

Cheveldayoff: There’s going to be challenges, no question. This is a challenge every team faces, and there will be tough decisions. But I’d rather have tough decisions.

Sportsnet: You just signed Wheeler, your captain, to a five-year, $41-million contract. That sure doesn’t look like a hometown discount compared to, say, Mark Scheifele’s long-term deal at $6.125 million per season.

Cheveldayoff: We paid what the market was for Mark Scheifele (in 2016). Nathan MacKinnon signed that summer. I think you’re always a function of the marketplace, really. Players have a right to unrestricted free agency. They earn their opportunities. With Blake, there’s so much more to him than just the player. But the player is very good.

Sportsnet: How uncomfortable are you that one of your top, young defencemen, Josh Morrissey, remains a restricted free agent a week before training camp?

Cheveldayoff: You always want your house in order. Hopefully, that falls into place shortly.

Sportsnet: He looks like a core player; will it be a long-term deal?

Cheveldayoff: We view him as a long-term Jet. However that falls into place, we’ll see.

Sportsnet: You’ve had difficult negotiations two times in three years with defenceman Jacob Trouba, who went to arbitration this summer to get a one-year contract. Do you view him as a long-term Jet?

Cheveldayoff: There’s been lot of different discussions that we’ve had with his group. The way this year worked out, with a one-year deal, I think it’s going to be beneficial to both sides.

Sportsnet: You took a chance making Connor Hellebuyck your starter, and rewarded his brilliant season with a new six-year, $37-million contract. What led you to go all-in on Hellebuyck?

Cheveldayoff: I think you have to take some chances along the way. One thing with Connor is he checked all the boxes in his development path. At different levels he has excelled. There are lots of leaps of faith you have to take in this game. No one is trading you a bonafide No. 1 goaltender in their prime. You have to allow them to develop.

There’s a cost to everything. If you sign a veteran player and block out a young player, there’s a cost to that as well. You might be marginally better in a short period, but exponentially worse in the long term. Sometimes you have to believe in your player.

Sportsnet: Everyone believes Patrik Laine will be a superstar in this league. Can you get an extension for him done now for less money than what he will cost to re-sign next summer?

Cheveldayoff: We’re open to everything. There are so many things that come into play that one simple answer doesn’t suffice. Again, Laine is a huge part of our organization and will be for many, many years to come. If (a contract) happens tomorrow, that’s great. If it happens a year from tomorrow, great.

Sportsnet: Will winning make Winnipeg a more favourable destination when trying to attract or retain top players?

Cheveldayoff: I’m not sure where we’ll land on players’ no-trade lists as we move forward, but that’s life. At the end of the day, Blake Wheeler said it best: ‘Is it cold in Winnipeg? Yeah. Is it a hockey environment? Absolutely.’

Is it a place you truly want to be immersed in a hockey market, with a great organization and great ownership and a coach who understands players? This is the place. We’re proud of what we’ve built and what we’re going to continue to build.

Sportsnet: Having gone to the conference final last May, are you excited about how close you are to challenging for a Stanley Cup this season?

Cheveldayoff: I think that’s a very dangerous type of feeling. I was reading something Mark Schiefele said: ‘Complacency is a silent death.’ You have to find a way to get better. That’s what drives us. There’s nothing guaranteed in this game. There are things around the bend that you try to anticipate, but you don’t know. It’s a hard league to win in. You have to earn it.

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